(3S)-3-[(R)-(4-chloro-2-methoxyphenoxy)-phenylmethyl]pyrrolidine | 1204673-49-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3S)-3-[(R)-(4-chloro-2-methoxyphenoxy)-phenylmethyl]pyrrolidine
• CAS: 1204673-49-3
• 化学式: C₁₈H₂₀ClNO₂
• 分子量: 317.815
• InChiKey: GIKANUDLIOICAL-KSSFIOAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S)-3-[(R)-(4-chloro-2-methoxyphenoxy)-phenylmethyl]pyrrolidine 、 三氟乙酸 以 水 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  A novel class of 3-(phenoxy-phenyl-methyl)-pyrrolidines as potent and balanced norepinephrine and serotonin reuptake inhibitors: Synthesis and structure–activity relationships

  摘要：

  A series of 3-(phenoxy-phenyl-methyl)-pyrrolidine analogues were discovered to be potent and balanced norepinephrine (NE) and serotonin (5-hydroxytryptamine, 5-HT) reuptake inhibitors. Several of these compounds were identified to have suitable in vitro pharmacokinetic properties for an orally dosed and CNS-targeted drug. Compound 39b, in particular, was identified as a potent NET and SERT reuptake inhibitor (NSRI) with minimal off-target activity and demonstrated robust efficacy in the spinal nerve ligation model of pain behavior. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.061
• 作为产物：
  描述：

  (S)-1-Boc-3-羟甲基吡咯烷 在 盐酸 、 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 偶氮二甲酸二异丙酯 、 碳酸氢钠 、 三苯基膦 、 potassium bromide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 18.42h， 生成 (3S)-3-[(R)-(4-chloro-2-methoxyphenoxy)-phenylmethyl]pyrrolidine
  参考文献：
  名称：

  A novel class of 3-(phenoxy-phenyl-methyl)-pyrrolidines as potent and balanced norepinephrine and serotonin reuptake inhibitors: Synthesis and structure–activity relationships

  摘要：

  A series of 3-(phenoxy-phenyl-methyl)-pyrrolidine analogues were discovered to be potent and balanced norepinephrine (NE) and serotonin (5-hydroxytryptamine, 5-HT) reuptake inhibitors. Several of these compounds were identified to have suitable in vitro pharmacokinetic properties for an orally dosed and CNS-targeted drug. Compound 39b, in particular, was identified as a potent NET and SERT reuptake inhibitor (NSRI) with minimal off-target activity and demonstrated robust efficacy in the spinal nerve ligation model of pain behavior. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.061

文献信息

• A novel class of 3-(phenoxy-phenyl-methyl)-pyrrolidines as potent and balanced norepinephrine and serotonin reuptake inhibitors: Synthesis and structure–activity relationships
  作者：Lori Jean Van Orden、Priscilla M. Van Dyke、D. Roland Saito、Timothy J. Church、Ray Chang、Jacqueline A.M. Smith、William J. Martin、Sarah Jaw-Tsai、Eric L. Stangeland

  DOI：10.1016/j.bmcl.2012.12.061

  日期：2013.3

  A series of 3-(phenoxy-phenyl-methyl)-pyrrolidine analogues were discovered to be potent and balanced norepinephrine (NE) and serotonin (5-hydroxytryptamine, 5-HT) reuptake inhibitors. Several of these compounds were identified to have suitable in vitro pharmacokinetic properties for an orally dosed and CNS-targeted drug. Compound 39b, in particular, was identified as a potent NET and SERT reuptake inhibitor (NSRI) with minimal off-target activity and demonstrated robust efficacy in the spinal nerve ligation model of pain behavior. (c) 2012 Elsevier Ltd. All rights reserved.